Synthesis and evaluations of new tetralone analogues of podophyllotoxin

Chaitramallu M*, Dakshayini C, Devaraju kesagodu
Department of Chemistry, University of Mysore, Yuvaraja’s College, Mysore-570006, Karnataka, India.

A B S T R A C T
The new tetralone (7a‐e) were synthesized as analogues of podophyllotoxin. They were prepared using 1-bromo-3, 4, 5‐trimethoxybenzene and aldehyde derivatives by Grignard reaction which is condensed with diethyl succinate by means of potassium tert-butoxide in tert-butyl alcohol yield 3 (a-e). Hydrolysis of 3(a-e) with HBr in refluxing acetic acid affords 4(a-e), which is hydrogenated with H₂ over Pd/C in ethyl acetate giving 5(a-e), which is converted into the corresponding acyl chloride with refluxing SOCl₂. Cyclization of 6(a-e) with AlCl₃ in dichloromethane yields 7(a-e). The structures of the synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass spectra and elemental analysis data. The synthesized tetralones were screened for their antimitotic activity.
Keywords: Tetralons, Grignard reaction, antimitotic assay